Chan, who was running Google Voice at the time, wanted to scupper
the deal. Levy reports that Chan thought the deal would be a
disaster because of antitrust and intellectual property issues.

There is still a good case to be made that Skype could have been
a good buy for Google. It's a huge network effects business that
would be a very nice complement to Google's business. Even today
Google works very hard to compete with Skype.

But what's interesting is less the merits than how Chan killed
the deal. In Chan's own phrase, he did it by "laying grenades,"
with the help of Google co-founder Sergey Brin. Chan told the
execs pushing for it that he supported the deal and worked with
them on presenting it. Then in the meeting to approve the deal
with Brin and CEO Eric Schmidt, Chan turned on his fellow execs,
arguing against it.

Then another exec declined to lead the integration because he had
two kids in school and didn't want to be travelling to Estonia,
where Skype is based.

Chan is now a partner at Google Ventures, the company's venture
capital arm, certainly not the worst gig in the world.

There's so much to unpack here:

It's startling to see that even in 2005, when Google
was still relatively young, this is how decisions were
reached. This is the kind of maneuvering by executives
to get their way that you expect to see at Microsoft or IBM,
not a Silicon Valley rocketship like Google, which prides
itself on reaching decisions through data.

What top exec at a top company doesn't want to lead a
deal because he might have to be travelling a lot? How
is that a valid argument at a company that's less than a
hundred years old?

It's also startling to see that Google's leaders didn't
see through a fairly obvious ruse. When someone comes
in to pitch a deal and suddenly turns against it, something is
up. Brin dismissed the deal out of hand because of a bad
meeting, not because of the fundamentals.

This story makes us understand new CEO Larry Page's big
reorg of the company much better. It seems like Google was,
and probably still is, rife with this kind of political, decision
by committee process. Page's drastic reorg wants to create more
accountability and speed by putting each division under a single
head. It seems that it's sorely needed.